the easiest way for me was to take my playlists from windows media player, export them to my usb drive, sort the playlists by folder, and copy it to the hard drive. the hard drive will copy the folders and each folder on the idrive is the playlist.

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"AMG What! S-Line Who? If you ain't got that M I got no respect for you!"

On my iPod, I have everything by it respectful Album Name. Then I have set up Playlist for everything else.
FOR PLAYLISTS: When you create the Playlist in iTunes, highlight all the songs in the playlist and make the Album Name & Album Artist the same for all the songs. For example, in iTunes, in the make a playlist called "Road Trip 1" and put 20 tracks or how ever many in this playlist. High-light all tracks to edit them all at once. Make the Album Name: Road Trip 1 and Album Artist: M3 Music.
This way you, when you connect your iPod to your iDrive, you can EASILY navigator thru your Albums and Playlists.

You guys will probably flame me because this sounds very old school and tedious...

On my computer, I have all my music titled "Artist, Featuring Artist - Track Title" and organized in separate folders for each alphabet. So, I created data CD-RW's for each alphabet and uploaded it onto the car, then renamed the default folder to "A"..."Z".

I simply avoid the problem, because I enjoy listening to the engine scream at high rpms. Since the audio system in my E90 is just the basic version, I find listening to music frustrating, so I just use it for news stations.

You can setup smart playlists in itunes as well. I use them to decide what goes on my ipod and what doesn't so I don't have to manually drag files in and out of my ipod.

I have a playlist that only accept albums with a rating of 3 stars or higher. Any album that is unrated, 1-star, or 2-star just stays on my computer.

the way I rate my albums is:
1-star: I pretty much don't like the album, and it's up for deletion consideration
2-star: Album only has a select songs that are worth listening to. In this case, I give a rating to the individual songs I like (giving them a 3-star or higher rating). This way only those songs are added to the ipod.
3-star: The entire album is worth listening to.
4-star: This is a good album that I like more than most.
5-star: All time favorite albums.

generally I have all albums rated, but sometimes I forget with new albums, and so I also have a smart playlist that adds my most recent additions to itunes to the ipod, so those are always accessible while they are new.

It only takes one click to rate, or change the rating of an album in iTunes, which compared to managing what is on the ipod manually saves a lot of time. If I decide to change an album rating from 3-stars to 1-star, it takes one click of the mouse, and will automatically be gone from the ipod on the next sync.

I use the iPod connector and I have a "New" playlist, where I put songs that I just downloaded into. I'm heavily involved with music/Dj'ing so I have all my stuff organized. Playlists are the best way to do it!

For the internal HDD, I got a bunch of spare USB thumb drives and put only one artist at a time on each drive and imported them individually. Renamed USB1, USB2, etc, automatically generated folders to the artist's name. Now at the root of the internal HDD, I have artist separation. If I want to change it up, now I can do it by artist, and not have to re-import another 12GiB. (though the music I put on the HDD is some of my all-time favorites, so I don't often switch it up).

For the USB in the console, I leave a 30GiB iPod in the console with tons of playlists. I also occasionally plug my iPhone in when it has some newer music I haven't had a change to sync to the iPod yet.

What is the comparative quality of playback between iPod with cable vs USB drive vs loaded to hard drive ? I know the bit rate quality of the track itself has great impact, but with all being equal on that, what is the preferred option.

I remember reading a thread stating there were varying levels of quality between these options.